Stereospecific nucleophilic substitution of optically active 1-benzyloxy-2,2,2-trifluoroethyl tosylate with lithium tetraalkylaluminates prepared by the Ti-catalyzed hydroalumination of olefins

Synlett

Volumn , Issue 12, 1998, Pages 1353-1354

  Matsutani, Hiroshi ^a   Poras, Hervé ^a   Kusumoto, Tetsuo ^a   Hiyama, Tamejiro ^b  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002656727     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1992     Document Type: Article

References (16)

1. For example: Hudlicky, M.; Pavlath, A. E., Eds.; Chemistry of Organic Fluorine Compounds II; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
2. Matsutani, H.; Poras, H.; Kusumoto, T.; Hiyama, T. Chem. Commun. 1998, 1259.
3. For the pioneering publication: Sato, F.; Sato, S.; Sato, M. J. Organomet. Chem. 1976, 122, C25.
4. For a review: Sato, F. In Fundamental research in homogeneous catalysis; Ishii, Y.; Tsutsui, M., Eds.; Plenum Press: New York, 1978; Vol. 2, p81.
5. Assignment of the absolute configuration of optically active 1-benzyloxy-2,2,2-trifluoroethyl sulfonate was discussed in ref 2,6.
6. Poras, H.; Matsutani, H.; Yaruva, J.; Kusumoto, T.; Hiyama, T. Chem. Lett., 1998, 665
7. 3) for 6b, respectively. The absolute configuration of 6c-e was estimated on the analogy of 6a and 6b.
8. The ratio of (% ee of 6)/(% ee of 4) as expressed in %.
9. For the substitution reaction at the carbon bearing a trifluoromethyl group by a heteroatom nucleophile, see: (a) Casara, P. J.; Kenny, M. T.; Jund, K. C. Tetrahedron Lett., 1991, 32, 3823;
10. (b) Hagiwara, T.; Tanaka, K.; Fuchikami, T. Tetrahedron Lett., 1996, 37, 8187;
11. (c) Mikami, K.; Yajima, T.; Terada, M.; Kawauchi, S.; Suzuki, Y.; Kobayashi, I. Chem. Lett., 1996, 861;
12. (d) Katagiri, T.; Ihara, H.; Takahashi, M.; Kashino, S.; Furuhashi, K.; Uneyama, K. Tetrahedron: Asymmetry, 1997, 8, 2933;
13. (e) Tongco, E. C.; Prakash, G. K. S.; Olah, G. A. Synlett, 1997, 1193;
14. (f) Ishii, A.; Miyamoto, F.; Higashiyama, K.; Mikami, K. Chem. Lett., 1998, 119.
15. A substitution reaction of a cyclic diastereomeric O,N-acetal having a trifluoromethyl group with organolithium reagents is reported to take place with retention: Ishii, A.; Miyamoto, F.; Higashiyama, K.; Mikami, K. Tetrahedron Lett., 1998, 39, 1199.
16. Sato, F.; Sato, S.; Sato, M. J. Organomet. Chem. 1977, 131, C26.